EP0720847A1 - Eine mindestens ein Ceramid 6 enthaltende kosmetische oder dermatologische Zubereitung - Google Patents

Eine mindestens ein Ceramid 6 enthaltende kosmetische oder dermatologische Zubereitung Download PDF

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Publication number
EP0720847A1
EP0720847A1 EP95402771A EP95402771A EP0720847A1 EP 0720847 A1 EP0720847 A1 EP 0720847A1 EP 95402771 A EP95402771 A EP 95402771A EP 95402771 A EP95402771 A EP 95402771A EP 0720847 A1 EP0720847 A1 EP 0720847A1
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EP
European Patent Office
Prior art keywords
ceramides
skin
composition
water
composition according
Prior art date
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Granted
Application number
EP95402771A
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English (en)
French (fr)
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EP0720847B1 (de
Inventor
Jean-Luc Leveque
Didier Saint-Leger
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LOreal SA
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LOreal SA
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/005—Preparations for sensitive skin

Definitions

  • the invention relates to a cosmetic or dermatological composition which comprises, as main agent for reducing the water loss of the skin and / or keratin fibers, at least one ceramide 6.
  • compositions which make it possible to prevent or correct these phenomena resulting in an apparent dryness and which give or restore to the skin its suppleness and to the hair its shine and softness.
  • ceramides are the predominant constituent elements of the intercoreocytic lipids of the stratum corneum and participate in maintaining the integrity of the skin barrier.
  • the ceramides used in cosmetics are always mixtures of different types of ceramides, their contents and their natures depending in particular on their origin and their extraction process.
  • the present invention is based on the discovery that it is, among the ceramides, the ceramides 6 which most allow to influence the phenomenon of reduction of water loss and which therefore make it possible to maintain or reproduce the barrier function of the skin of significantly.
  • the subject of the present invention is a cosmetic or dermatological composition, characterized in that it comprises at least one ceramide 6 as main agent for reducing the loss of water from the skin and / or keratin fibers.
  • ceramides 6 in a cosmetic or dermatological composition as a main agent for reducing the loss of water from the skin and / or keratin fibers.
  • the present invention applies to the skin.
  • Ceramides of types 1 to 6 are described by DOWNING in Arch. Dermatol, Vol. 123, 1381-1384, 1987. Ceramides of types 1 to 6 have the following structure:
  • ceramides 6 are phytosphingosines of two types: 6I or 6II.
  • the ceramides 6 used in the present invention can be ceramides of natural origin.
  • ceramide 6I or 6II is used alone or as a mixture, the mixture of ceramides 6 generally coming from the extraction of these from the mixture of ceramides present in the stratum corneum.
  • Ceramides 6, used in the present invention can be obtained by extraction of the stratum corneum from the skin of mammals, by any conventional method known per se, followed by progressive and selective delipidation, in particular by suitable solvents.
  • the skin of mammals can be the skin of humans, pigs, cattle, horses, sheep, goats, mice, rats, rabbits, dogs, guinea pigs, cats, monkeys, and the like.
  • the stratum corneum is isolated from the skin by conventional physicochemical methods.
  • the skin removed can be heated to temperatures in the region of 60 ° C., then treated with trypsin.
  • the progressive and selective delipidation making it possible to isolate the ceramides 6 is generally carried out by immersing the stratum corneum in one or more suitable solvents, such as in particular hexane, acetone, methanol, ethanol, chloroform and ethyl ether.
  • suitable solvents such as in particular hexane, acetone, methanol, ethanol, chloroform and ethyl ether.
  • suitable solvents such as in particular hexane, acetone, methanol, ethanol, chloroform and ethyl ether.
  • main agent for reducing water loss it is understood according to the invention that the minimum percentage by weight of ceramide 6 present in the composition relative to the total ceramides present as agents for reducing water loss in the composition is higher than its percentage by weight compared to the natural mixture of total ceramides from which it can come.
  • the percentage by weight of the 6I ceramides in the composition is greater than 9.8% (relative to the total weight of the ceramides present as an agent for reducing the loss in water in the composition) and / or the percentage by weight of the ceramides 611 in the composition is greater than 13.6% (relative to the total weight of the ceramides present as an agent for reducing water loss in the composition) .
  • the percentage of ceramides 6 present in the composition according to the invention is greater than 23.4% (relative to the total weight of the ceramides present as an agent for reducing water loss in the composition).
  • the minimum percentage by weight of the ceramides 6 present in the composition according to the invention is greater than 35%. Of course, this percentage can be higher and can reach 100%, the only agent for reducing the water loss present in the composition then being ceramides 6.
  • compositions according to the invention can be in the form of emulsions (milk or cream), hydroalcoholic, oily or oleoalcoholic lotions, gels, dispersions or solid sticks, sprays or aerosol foams.
  • the ceramides 6 generally represent from 0.01% to 20%, and preferably 0.05 to 10% of the total weight of the composition.
  • compositions are, for example, lotions, emollient milks or creams, milks or creams for skin or hair care, creams, lotions or cleansing milks, foundations, foundations, lotions, sunscreen milks or creams, lotions, artificial tanning milks or creams, shaving creams or foams, after shave lotions, shampoos or mascaras.
  • compositions can also be in the form of lip sticks intended either to color them or to prevent chapping, or make-up products for the eyes or eyeshadows and foundations for the face.
  • the fatty phase essentially consists of a mixture of ceramides 6 and at least one oil or a fatty substance.
  • the fatty phase of the emulsions can constitute 5 to 60% of the total weight of the emulsion.
  • the aqueous phase of said emulsions preferably constitutes 30 to 85% of the total weight of the emulsion.
  • the proportion of the emulsifying agent can be between 0.1 and 20%, and preferably between 1 and 12% of the total weight of the emulsion.
  • compositions according to the invention are in the form of oily, oleoalcoholic or hydroalcoholic lotions, they can constitute, for example, sunscreen lotions containing a filter absorbing UV rays, softening lotions for the skin; the oily lotions can also constitute foaming oils containing an oil-soluble surfactant, oils for the bath, etc.
  • fatty substances such as mineral or animal or vegetable oils or waxes, fatty acids, fatty acid esters such as triglycerides of fatty acids having from 6 to 18 carbon atoms, fatty alcohols; emulsifiers such as oxyethylenated fatty alcohols or polyglycerol alkyl ethers; solvents such as lower monoalcohols or polyalcohols containing from 1 to 6 carbon atoms or even water.
  • the more particularly preferred mono- or polyalcohols are chosen from ethanol, isopropanol, propylene glycol, glycerol or sorbitol.
  • Mention may be made, as fatty substance, of mineral oils, of petrolatum oil; among animal oils, whale, seal, menhaden, halibut, cod, tuna, turtle, ox's foot, horse's foot, sheep's foot, mink, otter's oils , groundhog, etc .; among vegetable oils, almond, wheat germ, olive, corn germ, jojoba, sesame, sunflower, palm, walnut, shea, shorea, macadamia, blackcurrant seeds and the like.
  • esters of saturated or unsaturated C12 to C22 acids and of lower alcohols such as isopropanol or glycerol or of saturated C8 to C22 fatty alcohols, linear or branched or unsaturated or alternatively 1,2-alkanediols C10-C22.
  • waxes mention may be made of Sipol wax, lanolin wax, beeswax, Candelila wax, monocrystalline wax, Carnauba wax, spermaceti, cocoa butter, shea butter, silicone waxes, hydrogenated oils concrete at 25 ° C, sucroglycerides, oleates, myristates, linoleates and stearates of calcium, magnesium and aluminum.
  • fatty alcohols mention may be made of lauric, cetyl, myristic, stearic, palmitic, oleic alcohols and GUERBET alcohols such as 2-octyldodecanol, 2-decyltetradecanol or 2-hexyldecanol.
  • emulsifiers among the polyoxyethylenated fatty alcohols, mention may be made of lauric, cetyl, stearyl and oleic alcohols comprising from 2 to 20 moles of ethylene oxide and among the glycerol alkyl ethers, C12-C18 alcohols comprising from 2 to 10 moles of glycerol.
  • thickeners such as cellulose derivatives, polyacrylic acid derivatives, guar or carob gum or xanthan gum.
  • composition according to the invention may also contain adjuvants usually used in cosmetics or dermopharmacy and in particular moisturizers, softeners, products for the treatment of skin conditions, sun filters, germicides, dyes, preservatives, perfumes and propellants.
  • adjuvants usually used in cosmetics or dermopharmacy and in particular moisturizers, softeners, products for the treatment of skin conditions, sun filters, germicides, dyes, preservatives, perfumes and propellants.
  • compositions according to the invention are dispersions, they may be dispersions of ceramides 6 in water in the presence of surfactant or alternatively aqueous dispersions of lipid spherules, consisting of organized molecular layers enclosing an encapsulated aqueous phase , these layers consisting of at least one ceramide 6 associated with at least one other lipid compound.
  • lipid compounds long chain alcohols and diols
  • sterols such as cholesterol, phospholipids, cholesteryl sulfate and phosphate, long chain amines and their quaternary ammonium derivatives, dihydroxyalkylamines, polyoxyethylenated fatty amines, esters of long chain amino alcohols, their salts and quaternary ammonium derivatives, phosphoric esters of fatty alcohols such as acid diketylphosphate or its sodium salt, alkylsulfates such as cetylsulfate sodium, fatty acids in the form of salts or lipids of the type described in French patents 2,315,991, 1,477,048 and 2,091,516 or in international patent application WO 83/01 571.
  • lipids comprising a long lipophilic chain containing 12 to 30 carbon atoms, saturated or unsaturated, branched or linear, for example an oleic, lanolic, tetradecylic, hexadecylic, isostearyl, lauric or alkylphenyl chain.
  • the hydrophilic group of these lipids can be an ionic or nonionic group.
  • nonionic groups mention may be made of groups derived from polyethylene glycol.
  • polyglycerol ethers such as those described in French patents Nos. 1,477,048, 2,091,516, 2,465,780 and 2,482,128.
  • ionic group it is advantageous to use a group derived from an amphoteric, anionic or cationic compound.
  • lipids described in international patent application WO 83/01 571 as being able to be used for the formation of vesicles are the glycolipids such as lactosylceramide, galactocerebroside, gangliosides and trihexosylceramide, as well as phospholipids such as phosphatidylglycerol and phosphatidylinositol.
  • the continuous phase of the dispersion which surrounds the spherules is an aqueous phase.
  • the spherules in dispersion generally have a diameter of between 0.05 ⁇ m and 5 ⁇ m.
  • the aqueous phase encapsulated in the spherules may be water or an aqueous solution of active substance and in this case is preferably isoosmotic with respect to the continuous phase of the dispersion.
  • the spherules can be obtained in particular according to the method described in French patent 2,315,991 of the Applicant, according to which a dispersion of spherules consisting of organized molecular layers containing an aqueous phase to be encapsulated, by bringing into contact on the one hand ceramides 6 associated with one or more lipid (s) defined above and on the other hand the aqueous phase to be encapsulated in the spherules, stirring to ensure mixing and obtaining a lamellar phase, then adding a dispersing liquid in an amount greater than the amount of lamellar phase obtained and shaking vigorously for a period ranging from 15 minutes to 3 hours approximately.
  • the weight ratio between the aqueous phase to be encapsulated and the ceramides 6 associated with the lipids forming the lamellar phase is preferably between 0.1 and 20.
  • the weight ratio of the aqueous dispersion phase which is added to the lamellar phase which is dispersed is preferably between 2 and 100, the dispersion phase and the aqueous phase to be encapsulated being preferably isoosmotic.
  • Agitation is carried out by means of a shaker.
  • the process is preferably carried out at a temperature between 30 ° and 120 ° C.
  • REV reverse-phase evaporation vesicle
  • reverse phase evaporation described in Proc. Natl. Acad. Sci. USA., Vol. 75, n ° 9, pages 4194-4198 (1978), by SZOKA and PAPAHADJOPOULOS.
  • the method which comprises the succession of steps consisting in dissolving at least one lipid in at least one organic solvent immiscible with water; adding the organic phase thus obtained to an aqueous phase; forming a dispersion of the two phases with vigorous stirring, the size of the vesicles being adjustable by varying the stirring speed during this phase mixing; conduct the evaporation of the solvent (s) under vigorous stirring; and, if necessary, concentrating the dispersion.
  • the active substances can be substances having a pharmaceutical or food interest or substances having a cosmetic activity. When they are water-soluble, they are in the aqueous phase encapsulated inside the vesicles.
  • the water-soluble substances having a cosmetic and / or pharmaceutical activity can be products intended for the care or treatment of the skin and the hair such as for example humectants such as glycerin, sorbitol, pentaerythritol, pyrrolidone carboxylic acid and its salts; artificial browning agents such as dihydroxyacetone, erythrulose, glyceraldehyde, ⁇ -dialdehydes such as tartaric aldehyde, these compounds being optionally combined with dyes; water-soluble sun filters; antiperspirants, deodorants, astringents, refreshing, tonic, healing, keratolytic, depilatory, scented waters; plant tissue extracts, such as polysaccharides; water-soluble dyes; dandruff agents; antiseborrhoeic agents, oxidants such as bleaching agents such as hydrogen peroxide; reducing agents such as thioglycolic acid and its salts.
  • the active substances are liposoluble, they are incorporated into the sheets of the vesicles. They can be chosen from the group formed by fat-soluble sunscreens, substances intended to improve the condition of dry or senile skin, tocopherols, vitamins E, F or A and their esters, retinoic acid, antioxidants, essential fatty acids, glycyrrhetinic acid, keratolytics and carotenoids.
  • the composition according to the invention may contain from 2 to 70% by weight of liquid phase L, immiscible with water, relative to the total weight of the composition, the relative weight proportion of lipid (s) ) constituting vesicles with respect to the dispersed liquid phase, L being between 0.02 / 1 and 10/1.
  • the constituent (s) of the liquid phase L dispersed in the aqueous phase D can (can) be chosen (s) from the group formed by oils, such as fatty acid esters of polyols and esters of fatty acid and branched alcohols of formula R 7 -COOR 8 , formula in which R 7 represents the remainder of a higher fatty acid containing from 7 to 19 carbon atoms and R 8 represents a branched hydrocarbon chain containing from 3 to 20 carbon atoms; hydrocarbons, such as hexadecane, paraffin oil, perhydrosqualene; halogenated hydrocarbons, such as perfluorodecahydronaphthalene; perfluorotributylamine; polysiloxanes; esters of organic acids, ethers and polyethers.
  • oils such as fatty acid esters of polyols and esters of fatty acid and branched alcohols of formula R 7 -COOR 8 , formula in which R 7 represents the remainder of a higher fatty
  • the liquid phase L can contain at least one perfume and / or at least one liposoluble active substance.
  • liposoluble substances can be constituted by liposoluble sunscreens, substances intended to improve the condition of dry or senile skin, tocopherols, vitamins E or F, vitamin A and its esters, retinoic acid, antioxidants , essential fatty acids, glycyrrhetinic acid, keratolytic agents and carotenoids.
  • the dispersions of lipid spherules have the advantage of carrying active substances which are thus masked and protected from the various spoilage agents: oxidants and more generally reactive compounds with respect to the encapsulated active substances.
  • the penetration and fixation of the active substances can be modulated by varying the size of the spherules and their electrical charge.
  • the action of its active substances can also be postponed (delay effect).
  • the invention finally relates to a cosmetic treatment process for the skin or keratin fibers, characterized in that it consists in applying to the skin or to the keratin fibers a composition as defined above. Since the composition according to the invention is well suited to moisturizing the skin, the cosmetic treatment process for the skin is more particularly intended for hydrating the skin.
  • composition of the invention can also be used in the treatment of xerosis and in any treatment of the skin where it is necessary to protect the skin.
  • compositions defined above for preparing an ointment or an ointment intended for the therapeutic treatment of dry skin.
  • the stratum corneum is isolated from the skin by the following method: heat to 58 ° C, then trypsin.
  • the samples are cut with a cookie cutter (10mm discs), identified and weighed before being mounted in the water loss tanks.
  • the measurement of the insensible water loss is done using an evaporimeter which is a device which quantitatively determines an evaporation of water, i.e. a transport of water by diffusion, from or towards surfaces in contact with the atmosphere.
  • the evaporimeter uses a combination of two sensors.
  • a small area of the skin is delimited by a cylindrical Teflon capsule.
  • the purpose of this capsule is to protect the measurement surface from drafts.
  • a pair of transducers one being a capacitor for measuring the relative humidity, the other a thermistor for measuring the temperature.
  • the instrument From the signals collected by this transducer, the instrument first calculates the partial pressure of the water vapor at the two points A and B then the partial pressure gradient and finally the evaporation rate (PIE).
  • the PIE of the stratum corneum taken at different stages of defatting was determined.
  • the progressive and selective delipidation making it possible to isolate the ceramides 6 is carried out by immersing the stratum corneum for approximately 30 minutes in hexane, then for approximately 60 minutes in acetone and finally in a chloroform / methanol mixture for approximately 120 minutes.
  • the initial PIE that is to say before any delipidation step, is 1.14 ⁇ 0.3 g / m 2 .H.
  • the ceramides 6 thus extracted can be formulated as described in the following examples.
  • the emulsion is in the form of a white cream to be applied in the evening to repair and hydrate the skin. It is intended for all skin types.
  • This emulsion is a white day cream, moisturizing, usable for all skin types.
  • This cream is more specifically intended for the night treatment of sensitive dry skin.
  • Example 5 Hydrating water-in-oil emulsion
  • This cream is more specifically intended for the night treatment of dry skin.
  • This gel is intended for hydration and restructuring of dry skin.
  • This gel is intended for the hydration of the body of all skin types.
  • This gel is rather intended for the hydration of the body of sensitive skin.
  • This gel is rather intended for hydration and restructuring of dry skin, especially at night.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
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  • Engineering & Computer Science (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP95402771A 1995-01-04 1995-12-11 Eine mindestens ein Ceramid 6 enthaltende kosmetische oder dermatologische Zubereitung Revoked EP0720847B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9500045 1995-01-04
FR9500045A FR2728792A1 (fr) 1995-01-04 1995-01-04 Composition cosmetique ou dermatologique comprenant au moins un ceramide 6

Publications (2)

Publication Number Publication Date
EP0720847A1 true EP0720847A1 (de) 1996-07-10
EP0720847B1 EP0720847B1 (de) 1997-09-10

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EP95402771A Revoked EP0720847B1 (de) 1995-01-04 1995-12-11 Eine mindestens ein Ceramid 6 enthaltende kosmetische oder dermatologische Zubereitung

Country Status (9)

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EP (1) EP0720847B1 (de)
JP (1) JP2962670B2 (de)
AT (1) ATE157863T1 (de)
CA (1) CA2166517C (de)
DE (1) DE69500695T2 (de)
DK (1) DK0720847T3 (de)
ES (1) ES2109793T3 (de)
FR (1) FR2728792A1 (de)
GR (1) GR3025136T3 (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2750046A1 (fr) * 1996-06-19 1997-12-26 Oreal Compositions sous forme d'un gel aqueux comprenant un ceramide ou un compose de type ceramide
US5882661A (en) * 1997-03-12 1999-03-16 Elizabeth Arden Co., Division Of Conopco, Inc. Composition and method for topical application to skin, hair and nails
US6063387A (en) * 1997-04-17 2000-05-16 Elizabeth Arden Co., Division Of Conopco, Inc. Anhydrous cosmetic composition with ceramides for firming skin
EP1036556A2 (de) * 1998-11-24 2000-09-20 GOLDWELL GmbH Verwendung von Ceramiden zur Haarpflege
CN109843257A (zh) * 2016-10-14 2019-06-04 株式会社大赛璐 化妆品组合物

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
JP5247127B2 (ja) * 2006-11-29 2013-07-24 第一三共ヘルスケア株式会社 セラミド類を含有する油中水型乳化物

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JPS61260008A (ja) * 1985-05-15 1986-11-18 Sunstar Inc 化粧料組成物
FR2679770A1 (fr) * 1991-08-01 1993-02-05 Oreal Dispersions cationiques pour le traitement des cheveux ou de la peau a base de ceramides et/ou de glycoceramides, compositions cosmetiques les renfermant et leurs applications cosmetiques.
WO1993020038A1 (en) 1992-04-03 1993-10-14 Gist-Brocades N.V. Selective n-acylation of amino alcohols
FR2700953A1 (fr) * 1993-01-29 1994-08-05 Sederma Sa Utilisation de certaines souches de microorganismes comme nouvelle source de céramides et de sphingolipides pour usage cosmétique.

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FR2676936B1 (fr) * 1991-05-27 1993-11-05 Inocosm Laboratoires Procede de separation d'un compose riche en glycolipides lysophospholipides shingolipides et ceramides d'origine vegetale, ainsi que produits cosmetiques obtenus par la mise en óoeuvre de ce procede.
GB9220268D0 (en) * 1992-09-25 1992-11-11 Unilever Plc Cosmetic composition
US5368857A (en) * 1993-11-15 1994-11-29 Elizabeth Arden Company, Division Of Conopco, Inc. Ceramide cosmetic compositions
JPH08512060A (ja) * 1994-04-27 1996-12-17 ギスト ブロカデス ベスローテン フェンノートシャップ 短鎖２−ヒドロキシカルボン酸をベースにしたセラミド誘導体
FR2719216B1 (fr) * 1994-05-02 1996-05-31 Oreal Composition pour le traitement et la protection des cheveux à base de céramides et de polymères de Vinylpyrrolidone.
EP0741562A1 (de) * 1994-11-28 1996-11-13 Gist-Brocades B.V. Topische Verwendung von Ceramiden

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61260008A (ja) * 1985-05-15 1986-11-18 Sunstar Inc 化粧料組成物
FR2679770A1 (fr) * 1991-08-01 1993-02-05 Oreal Dispersions cationiques pour le traitement des cheveux ou de la peau a base de ceramides et/ou de glycoceramides, compositions cosmetiques les renfermant et leurs applications cosmetiques.
WO1993020038A1 (en) 1992-04-03 1993-10-14 Gist-Brocades N.V. Selective n-acylation of amino alcohols
FR2700953A1 (fr) * 1993-01-29 1994-08-05 Sederma Sa Utilisation de certaines souches de microorganismes comme nouvelle source de céramides et de sphingolipides pour usage cosmétique.

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Title
PATENT ABSTRACTS OF JAPAN vol. 11, no. 115 (C - 415)<2562> 10 April 1987 (1987-04-10) *
PHILIP W. WERTZ ET AL, ARCHIVES OF DERMATOLOGY, vol. 123, no. 10, pages 1361 - 1363 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2750046A1 (fr) * 1996-06-19 1997-12-26 Oreal Compositions sous forme d'un gel aqueux comprenant un ceramide ou un compose de type ceramide
US5882661A (en) * 1997-03-12 1999-03-16 Elizabeth Arden Co., Division Of Conopco, Inc. Composition and method for topical application to skin, hair and nails
US6063387A (en) * 1997-04-17 2000-05-16 Elizabeth Arden Co., Division Of Conopco, Inc. Anhydrous cosmetic composition with ceramides for firming skin
EP1036556A2 (de) * 1998-11-24 2000-09-20 GOLDWELL GmbH Verwendung von Ceramiden zur Haarpflege
EP1036556A3 (de) * 1998-11-24 2001-08-29 GOLDWELL GmbH Verwendung von Ceramiden zur Haarpflege
CN109843257A (zh) * 2016-10-14 2019-06-04 株式会社大赛璐 化妆品组合物
EP3527193A4 (de) * 2016-10-14 2020-07-29 Daicel Corporation Kosmetische zusammensetzung
US10933004B2 (en) 2016-10-14 2021-03-02 Daicel Corporation Cosmetic composition

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Publication number Publication date
EP0720847B1 (de) 1997-09-10
FR2728792B1 (de) 1997-02-14
DE69500695T2 (de) 1998-01-15
ES2109793T3 (es) 1998-01-16
FR2728792A1 (fr) 1996-07-05
JPH08231338A (ja) 1996-09-10
CA2166517C (fr) 2001-12-25
ATE157863T1 (de) 1997-09-15
JP2962670B2 (ja) 1999-10-12
CA2166517A1 (fr) 1996-07-05
DK0720847T3 (da) 1998-02-23
GR3025136T3 (en) 1998-02-27
DE69500695D1 (de) 1997-10-16

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